@secondcor521 - it turns out that I actually read your journal a while back. It was good. I liked the idea of using multiples of monthly expenses to avoid posting raw dollar amounts.
@CowboyAndIndian - Dr. Doom is interesting. He seemed well prepared back in 2014 and 2015. But then the update in 2021 of his health troubles, along with the divorce torpedoing his financial plans was instructive. The "superplan" may not work when the variables change. My first thoughts about this are
1) to try to game out a few common ways things can go wrong and see if there are reasonable contingency plans for those cases (along these lines - invest in time with your friends and your partner, before troubles start)
2) understand that it's just not going to be possible to plan for everything - be prepared, but to also be flexible
3) that going back to work may not be a personal failure.
So it's
more about wayfinding and less navigation (Designing Your Life talk link).
I have a copy of World & Time Enough now too.